Rogue 101: A Beginner’s Guide to Stealth and Subterfuge

Rogue 101: A Beginner’s Guide to Stealth and Subterfuge

The rogue gulped down air as he ran through the dungeon corridor, his panicked party lagging two dozen feet behind him. The shrieks and war cries of the orc warband pursuing them echoed down the ancient halls. Only one hundred feet of dwarvencraft tunnels and a few blind turns separated the exhausted dungeon delvers from the howling horde—and certain death.

The rogue skidded to a breathless halt as he turned another corner. He grimaced and wiped a bead of sweat from his brow—the iron door he was looking at hadn’t been shut when they entered the dungeon. Sometime between the start of their delve and now, the orcs had closed the door to their cavern, wrapped it in chains, and secured it with a crude padlock. The rogue took a few steps forward to examine the lock… and grunted with pain as he was struck from behind. He slammed face first into the door, his vision exploding into starbursts of pain.

“Eyes ahead, you ape!” the rogue groaned, regaining his footing. He turned and affixed his party’s fighter with a murderous look. The rest of the party had rounded the corner, and he thanked Tymora that at least the wizard and the cleric had a little grace.

“We’re cornered, little guy,” the fighter gasped, her voice shaking. Blood dripped slowly through the steel scales of her armor, staining her tabard a deep red. The rogue felt a twinge of remorse and his steely gaze softened.

“I’ve been reduced to cantrips,” the gnome wizard said with a scowl. He tugged anxiously at his beard as he stepped level with the fighter, the tip of his pointed hat barely reaching her waist. “I admit the situation seems hopeless.”

“I think I have one more cure or guiding bolt left in me,” the cleric sighed, instinctively running her prayer beads through her fingers. “But that won’t do much against…”

Her words stopped dead in her throat as another chorus of war-shrieks shot through the hallway.

As if to calm his panicked companions, the rogue produced a bent set of thieves’ tools with a dramatic flourish from one of the two dozen tiny pouches concealed on his person. He craned his neck to meet the fighter’s eye and gave her a grin as crooked as his lockpick. “Don’t worry, love. I never pick a fight I can’t run away from.”

You are a rogue, a scoundrel, a charlatan. Perhaps you acquire gold by picking pockets, or perhaps you instead earn it as a practitioner of the foul art of murder, as an assassin with a wealthy patron. You may have underworld connections with the Zhentarim or the Xanathar Guild, or you may simply be a street urchin that has learned to survive by picking pockets.

The rogue as presented in the fifth edition Player’s Handbook is a nimble hit-and-run warrior that does incredible burst damage in combat—but that also possesses invaluable out-of-combat skills such as picking locks, disarming traps, and communicating in code. Depending on your choice of Roguish Archetype, you may gain other abilities such as manifesting magical illusions, designing flawless disguises, and performing incredible feats of acrobatics.

This guide covers the basics of being a rogue, and will walk you through the first 5 levels of this class, focusing on what equipment a rogue needs, how to improvise like a scoundrel, and how to make the most of your class features.

Quick Build Expanded: Building Your Rogue

This isn’t a character optimization guide, but the first step in playing your class effectively is building it effectively. The Quick Start guidelines in the Player’s Handbook are a good start, but don’t go far enough for most new players. Here’s an expanded Quick Start guide. This guide assumes you’re using the D&D Beyond Character Builder, which includes helper text for new players.

Choose your Race. While any race can be a good rogue, you may want to choose a race that improves your Dexterity score.

Halflings make excellent rogues because they grant you a racial bonus to Dexterity, a rogue’s most valuable ability score. Lightfoot halflings also gain the Naturally Stealthy trait, which lets you hide behind creatures that are larger than you, such as your human-sized party members!

Elves are outstanding rogues as well for similar reasons. They gain a racial bonus to Dexterity, and wood elves also gain the Mask of the Wild feature, allowing them to easily hide in the natural world.

Forest gnomes are a rare choice, but make for exceptional Arcane Trickster rogues, thanks to their bonus to Dexterity and their ability to manifest simple illusions thanks to their Natural Illusionist feature.

Tieflings have some useful roguish racial features too. Not needing light to see makes it easier to hide, and thaumaturgy is a neat tool to make a distraction... possibly allowing you to sneak into or out of a guarded location.

Choose rogue as your class (obviously).

Choose skills that fit the character you want to play. A dashing, Han Solo-like scoundrel would want to be proficient in the Deception skill, whereas a razor-sharp investigator like Sherlock Holmes would want to be proficient in the Investigation skill. Rogues get lots of different skills, so feel free to take some unusual ones that support your unique character!

Two skills that almost all rogues want, however, are Perception and Stealth. Since all rogues are skilled with thieves’ tools, you will probably be expected to disarm traps on treasure chests and doors. You’ll need a good bonus to Wisdom (Perception) checks in order to spot these traps. Also, you’ll probably be sneaking around a lot as a rogue, and having a good bonus to Dexterity (Stealth) checks will make your life much easier.

Place your highest ability score in Dexterity. The best place to put your second highest ability score depends on which Roguish Archetype you want to pick at 3rd level, but you can just as easily place it wherever you want.

If you want to play a Thief or an Assassin (or a Scout from Xanathar’s Guide to Everything), put your second highest ability score in Wisdom. Select Intelligence if you’re thinking of playing an Arcane Trickster or an Inquisitive from Xanathar’s Guide to Everything. Or finally, select Charisma if you plan on playing a Swashbuckler from Xanathar’s Guide to Everything.

Choose any background that fits your character concept.

Finally, choose your equipment by clicking on “EQUIPMENT” when prompted to “Choose EQUIPMENT or GOLD”. Choose:

A rapier if you want to fight with a one-handed weapon, or a short sword if you want to dual wield.

A shortbow if you want to also be able to fight from range, or another short sword if you want to dual wield.

A burglar’s pack if you think you’ll be spending time in cities, a dungeoneer’s pack if you think you’ll be exploring ancient ruins, or an explorer’s pack if you think you’ll be spending a lot of time traveling.

Leather armor, two daggers, and thieves’ tools (no choice to be made here).

What Kind of Rogue are You?

As a rogue, your skillset is an unusual mix of incredible offensive power and out-of-combat utility. As noted by fifth edition D&D's co-creator Mike Mearls, rogues are defined more by their core class features than their subclass (“Roguish Archetype”) features. Rogues of all subclasses fall into a role that is a mix of Offense and Support roles. If you’re able to land a sneak attack on every single turn (either through clever tactics or through teamwork), you will probably have the best damage-per-round ratio of any character in the party.

You’ll probably need protection from other characters in the party to survive after leaping heedlessly into the fray, but you still have plenty of ways to mitigate damage if your party isn’t there to tank hits for you. While you can’t wear heavy armor, a set of studded leather and a high Dexterity score will grant you a respectable AC 15 at 1st level (assuming a +3 Dexterity), and your Cunning Action and Uncanny Dodge features (which you gain at 2nd and 5th level, respectively) grant you even more personal defensive power.

While all rogues are a fairly even mix of Offense and Support, your choice of Roguish Archetype at 3rd level will affect your role somewhat. Thief and Arcane Trickster rogues are more Support-oriented (though neither gain buff or healing abilities like a cleric), while Assassin rogues are more Offense-focused.

(And note, I’m using Offense, Tank, and Support as shorthand. No part of D&D refers to characters in this way, but it’s an easy way to discuss the different roles characters serve in the party.)

Fighting like a Rogue

Most rogues play more or less the same for the first two levels, and only start to diverge once they choose a Roguish Archetype at 3rd level. However, your choice of weapons and preference towards Offense or Support will play a significant role in what your rogue excels at, both in and out of combat.

At 1st level, you gain one of your most important roguish tools, Sneak Attack. This feature is worded in a somewhat confusing way, so here’s a simplified reading of Sneak Attack:

“Whenever you have advantage on an attack roll, you deal Sneak Attack damage. You also deal Sneak Attack damage when an ally is adjacent to a creature you’re attacking. However, you never deal Sneak Attack damage when you have disadvantage on an attack roll. Your Sneak Attack damage is listed in the “Sneak Attack” column of your class table.”

Also at 1st level, you gain the Expertise feature, which lets you double your proficiency bonus to two skills or tools of your choice. Gaining expertise in the Stealth skill and thieves’ tools is always a good choice, but it’s up to you to determine what your favorite skills are.

Also at 1st level, you learn thieves’ cant, a secret language spoken only by rogues and other folk with a criminal past. This feature is only as useful as you and your DM (or other rogue players in your party!) make it. It could be crucial to breaking a secret cipher in a thief-centric arc… or it could never come up even once in play. If you want to make this ability useful and your DM isn’t giving you an opportunity to use it, you should talk with your DM and work out a thief-centric story together.

At 2nd level, you gain a feature that is often underrated by new players, Cunning Action. This feature lets you use your bonus action to Dash, Disengage, or Hide. You can use this bonus action every single turn if you want to, granting you some incredible utility in combat.

By dashing, you could conceivably run up to 90 feet in a single round if you use your normal movement, Dash as an action, and then Dash again as a bonus action (assuming you have a movement speed of 30 feet).

By disengaging, you can run straight through a room full of enemies straight towards the door by dashing as an action and disengaging as a bonus action. You could also run in, attack as action, and then disengage to escape as a bonus action (if you have enough speed to move that far).

By hiding, you can pop out of cover, sneak attack a foe (remember that you have advantage on attacks against foes that aren’t aware of you), and then duck back behind cover and hide again.

At 3rd level, you get to choose a Roguish Archetype. There are three in the Player’s Handbook (Thief, Assassin, and Arcane Trickster) and four in Xanathar’s Guide to Everything (Inquisitive, Mastermind, Scout, and Swashbuckler). All of these subclasses feature a mix of Offense and Support options, but some lean more in one direction or the other.

Offense

As a rogue that wants to increase their damage, you should choose one of the following archetypes: Assassin, Inquisitive (XGE), Scout (XGE), or Swashbuckler (XGE).

At 3rd level as an Assassin, you gain the Assassinate feature, making it easier to sneak attack creatures in the first round of combat, and allowing you to critically damage creatures that are surprised by you. Note that surprising a creature is different from having sneak attack or having advantage. You can’t surprise a creature if it’s aware of your presence in any way.

At 3rd level as an Inquisitive, you gain the Ear for Deceit and Eye for Detail features. Ear for Deceit makes you more reliable in social situations, and Eye for Detail lets you swiftly notice hidden creatures, traps, and clues in combat situations. You also gain the Insightful Fighting feature, which lets you sneak attack any creature as long as you are able to make a successful contested Wisdom (Insight) check.

At 3rd level as a Scout, you gain the Skirmisher feature, allowing you to stay mobile on the battlefield. This allows you to be more aggressive in combat situations, freeing up your bonus action to Dash instead of relying on Disengage to get out of tough spots. You also gain the Survivalist feature, which grants you some potent skill proficiencies for surviving in the wilderness.

At 3rd level as a Swashbuckler, you gain the Fancy Footwork and Rakish Audacity features, allowing you to be a lone wolf in combat. Fancy Footwork lets you move around creatures that you make melee attacks against (even on a miss!) without provoking opportunity attacks, and Rakish Audacity grants you Sneak Attack damage when attacking creatures with neither allies nor enemies around it. While some rogues must rely on their party to help set up sneak attack situations, you are free to roam the battlefield (or dungeon corridors), taking out exalted targets with ease.

Support

As a rogue that wants to help your party or otherwise make mischief, you should choose one of the following archetypes: Thief, Arcane Trickster, or Mastermind (XGE).

At 3rd level as a Thief, you gain Fast Hands and Second-Story Work, two nifty abilities that make it easier for you to infiltrate places quickly. Fast Hands even lets you chug a potion (using the Use an Object action) as a bonus action, allowing you to attack on the same turn!

At 3rd level as an Arcane Trickster, you gain the ability to cast spells. You should learn the friends and minor illusion cantrips, and the color spray, disguise self, and Tasha’s hideous laughter spells. Disguise self makes it easier to infiltrate locations and deceive others, color spray is a useful distraction when you need to escape combat, and Tasha’s hideous laughter is a simple way to gain advantage (and thus sneak attack) against troublesome enemies.

At 3rd level as a Mastermind, you gain the Master of Intrigue feature, allowing you to mimic other creatures and granting you a lot of extra proficiencies. You also gain the Master of Tactics feature, which lets you Help your allies from a distance as a bonus action. This lets you use your bonus action offensively to help your team instead of defensively to save your own hide.

At 4th level, you gain an Ability Score Increase. You should increase your Dexterity score by 2. If you decide to take a feat instead, the Lucky feat is an excellent pick for rogues. The Lucky feat makes it more likely for individual important rolls to succeed, and since you can only make one attack per turn, you really want to make it count.

Mounted Combatant is a particularly cheesy feat, since it grants you advantage on unmounted creatures that are smaller than your mount while you’re mounted. A rogue on horseback (or dragonback!?) can always sneak attack other humans that aren’t mounted! A situational feat, yes, but very powerful in its specific situation.

Also at 4th level as an Arcane Trickster, you should learn the silent image or sleep spell. Choose silent image if you want to focus on Support, or sleep if you want to be better at Offense.

At 5th level, you gain the Uncanny Dodge feature, which allows you to use your reaction to halve the damage of one attack made against you by a creature that you can see! While this feature has no effect on spells and abilities that don’t make attack rolls (that’s the job of Evasion, at 7th level), this is a huge upgrade to your defensive abilities. You can only use it once per round since it requires your reaction, but you should use it early and often. Since this feature can essentially be used every turn of combat, you would much rather use it early than “waste” your use of it.

Improvising like a Rogue

Class features, feats, and ability scores are only a tiny part of what makes a rogue—or indeed, any D&D class—fun to play. Rules are important because they set baseline expectations, but D&D comes to life when you take your life into your own hands and start to improvise exciting actions on the fly. Rogues are particularly suited to this sort of gutsy improvisation for several reasons. In the fiction of the game, rogues don’t play by the rules. They fight dirty. And most importantly, they have the gumption to leap before they look, often surviving impossible situations by the skin of their teeth.

The narrative identity of a devil-may-care rogue is modeled in D&D by granting rogues lots of skill proficiencies and even granting Expertise on top of that. I would recommend taking the Lucky feat on top of all of those bonuses, just in case the dice decide to ruin your creative ambitions. The danger of this system, however, is the DM. The best DMs know that it’s better to let you take wild risks, even if they have only a minimal chance of success, because spectacular failure is often just as fun as victory against all odds.

If your DM is hesitant to allow improvised actions, the only way to work it out is to talk directly with them. There’s no rules quirk or clever roguish trick more effective than just talking. If you’re playing in the D&D Adventurer’s League, which adheres strictly to the official D&D rules, you may have less luck.

Improvising Stunts

Improvised weapons are present in the D&D rules, but using one is almost always less effective than using the weapons with which you’re proficient. While improvised weapons are of limited use to the enterprising rogue, improvising a dirty trick or stunt while in combat is another matter!

House Rule: Combat Stunt

As an action (or in place of a single attack if you can attack multiple times when you take the Attack action), you can make a DC 15 ability check. You must propose which ability and skill proficiency you use to make this check to the DM before you make it, and can only perform this check with the DM’s approval.

If you succeed on this check, you can make a single weapon attack or a Dexterity (Stealth) check with advantage. If you fail this check, you waste your action. For instance, while in the jungle, you can make a Dexterity (Acrobatics) check to swing from a vine and attack a creature on the other end of a chasm. In the desert, you could make a Strength (Athletics) check to kick up a cloud of sand and duck behind cover as the enemy blinks sand out of its eyes. Or, while in an echoey cave, you could make a Charisma (Deception) check to throw your voice and convince an enemy that you are approaching to attack it from a different direction.

The best stunts are used once and thrown away. From an in-universe standpoint, using an improvised attack as a standard tactic defeats the purpose of using the situation at hand to your advantage. From a gameplay perspective, using the same tactic over and over again just becomes boring for your friends. You should try and come up with your own stunts on the fly (that’s the whole point of improv and fast thinking!).

Making your Rogue your Own

For the most part, this guide focuses on the rules of D&D and how to use them to your advantage. With all this talk of rules and stats and bonuses, don’t forget that your character is more than just prescribed actions. Your character has a personality that should impact how you play. If dealing the most damage isn’t what makes you happy about playing D&D, try and decide what does. Coming up with jokes, making cinematic moments, and making your fellow players cheer when you succeed are all worthy goals for a D&D player. You could even get deadly by using alchemy and poisons... though that's more like Rogue 102.

This guide is a little looser than other classes because personality and improvisation are central to the identity of a rogue. Embrace your lawless side and don’t be afraid to break some rules (if you and your DM agree to it). That way, even if you make the most paint-by-numbers rogue ever conceived, you’ll still have enough personality and panache to make them stand out from the crowd.

James Haeck is the lead writer for D&D Beyond, the co-author of the Critical Role Tal'Dorei Campaign Setting, and a freelance writer for Wizards of the Coast, the D&D Adventurers League, and Kobold Press. He lives in Seattle, Washington with his fuzzy sneak-attackers, Mei and Marzipan. You can usually find him wasting time on Twitter at @jamesjhaeck.

I have a question regarding cunning action/hide bonus action during combat. Your guide says:At 2nd level, you gain a feature that is often underrated by new players, Cunning Action. This feature lets you use your bonus action to Dash, Disengage, or Hide. You can use this bonus action every single turn if you want to, granting you some incredible utility in combat.

My DM says it doesn't make sense that a rogue can, after attacking, duck back behind cover and use his bonus action to hide, setting up an attack with advantage on his next turn. If that's true, what is the purpose of the Hide bonus action during combat as part of the Cunning Action ability?

Notice the language here: Lv. 2 Cunning Action: Dash, Disengage or Hide as a bonus action. Simply one of the best features in the game. Dart in, attack in melee, Disengage and move out. Or cover twice the real estate other characters would with a full move and a Dash, darting well out of the movement capabilities of most melee enemies while you hit and run them to death. Or while hidden: Attack, move, Hide and repeat, getting advantage on every attack.

So many possibilities, all of them exciting and keeping you on the move and hard to pin down. Under the arcane trickster section: Magical Ambush: Lv. 9. Invoke disadvantage on saving throws against your spells from hiding. In the Rogue's typical Hidden, Shoot, Move, Hide, Repeat routine, you can replace the "Shoot" part with "Cast" and really mess up an encounter with a couple of choice hard-to-resist spells (ahem, Suggestion).

My opinion is that this is one of the main features of the rogue, one that makes the rogue worth playing. I also think it's situational. Based on the situation (e.g. how many allies you have to distract the enemy, how much/good cover is available, etc) the DM should impose disadvantage on the stealth roll and/or give the enemy advantage on their perception roll as appropriate. I also suggested make it progressively more difficult to continue to use this attack against the same group of foes. Maybe impose disadvantage to remain hidden when breaking cover to attack on round 2, then also give the enemy advantage on their perception roll on round 3. This accounts for them catching on to your sneaky little tricks as the fight progresses.

This feature lets you use your bonus action to Dash, Disengage, or Hide. You can use this bonus action every single turn if you want to, granting you some incredible utility in combat.

My DM says it doesn't make sense that a rogue can, after attacking, duck back behind cover and use his bonus action to hide, setting up an attack with advantage on his next turn. If that's true, what is the purpose of the Hide bonus action during combat as part of the Cunning Action ability?

The enemy saw where you attacked from and can follow you around the corner, negating your hiding spot.

Hiding can fail (you need to roll Stealth and beat the passive Perception of every enemy.)

Even when hiding succeeds, if one enemy takes the Search action and beats your stealth check, you're no longer hidden. Only one enemy has to succeed to negate your advantage.

Gaining advantage on 1 attack roll isn't much better than simply attacking twice, which a Rogue could choose to do every turn with two-weapon fighting (or Crossbow Expert.)

A melee Rogue can't attack, disengage, and hide in the same turn.

Overall, it's a valid strategy, with its own advantages and disadvantages over running in, attacking and disengaging, or staying in melee range and using two-weapon fighting. Of course, you can change strategies depending on the situation.

Thanks, that's pretty much my understanding as well. As you said a melee rogue cannot both disengage and hide with his bonus action so I would really see this mainly being a peek-around-cover, take a ranged attack, duck-back-behind-cover, and hide scenario.

Are you sure that's true? From the PHB: When a creature can't see you, you have advantage on attack rolls against it. Can you point me to where it says anything about a creatures allies seeing you negates this?

Thanks, that's pretty much my understanding as well. As you said a melee rogue cannot both disengage and hide with his bonus action so I would really see this mainly being a peek-around-cover, take a ranged attack, duck-back-behind-cover, and hide scenario.

Yup. An enemy that's in combat would see you walking out of cover anyways. If you somehow had heavy obscurement that doesn't blind you within melee reach an enemy you wouldn't need to hide anyways; you'd already have advantage from being an unseen attacker, and they can't take an opportunity attack against an enemy they can't see.

Thanks, that's pretty much my understanding as well. As you said a melee rogue cannot both disengage and hide with his bonus action so I would really see this mainly being a peek-around-cover, take a ranged attack, duck-back-behind-cover, and hide scenario.

Yup. An enemy that's in combat would see you walking out of cover anyways. If you somehow had heavy obscurement that doesn't blind you within melee reach an enemy you wouldn't need to hide anyways; you'd already have advantage from being an unseen attacker, and they can't take an opportunity attack against an enemy they can't see.

Not necessarily. From the PHB: In combat, most creatures stay alert for signs of danger all around, so if you come out of hiding and approach a creature, it usually sees you. However, under certain circumstances, the Dungeon Master might allow you to stay hidden as you approach a creature that is distracted, allowing you to gain advantage on an attack before you are seen.

Clearly this is situational. The point that I am trying to make is that once the rogue breaks line-of-sight and successfully hides (via a contested stealth/perception check), they should have a "chance" of staying hidden when breaking cover (if the situation warrants it, like the enemy is busy trying to avoid getting stabbed by my allies). Just because they know where I went doesn't mean they no where I am after I hide or will notice me when I pop out on the other side of the tree/column/etc.

Also, what seems to be overlooked is that rogues excel at hiding the way a wizard excels at spellcasting. This is a special ability of rogues that they can do better than any other character and the cunning action "hide during combat as a bonus action" was obviously put in there for a reason. You are essentially neutering the rogue if you take that ability away.

Impose disadvantage if you think the odds aren't favorable they will remain hidden but don't arbitrarily change the RAW to say they can't even try to do it.

Yup. An enemy that's in combat would see you walking out of cover anyways. If you somehow had heavy obscurement that doesn't blind you within melee reach an enemy you wouldn't need to hide anyways; you'd already have advantage from being an unseen attacker, and they can't take an opportunity attack against an enemy they can't see.

Not necessarily. From the PHB: In combat, most creatures stay alert for signs of danger all around, so if you come out of hiding and approach a creature, it usually sees you. However, under certain circumstances, the Dungeon Master might allow you to stay hidden as you approach a creature that is distracted, allowing you to gain advantage on an attack before you are seen. Clearly this is situational. The point that I am trying to make is that once the rogue breaks line-of-sight and successfully hides (via a contested stealth/perception check), they should have a "chance" of staying hidden when breaking cover (if the situation warrants it, like the enemy is busy trying to avoid getting stabbed by my allies).

Every enemy's trying not to get stabbed in combat. I'm pretty sure the PH is talking about being distracted by some other task, like picking a lock or disarming a trap. You know, something that'd actually take your attention away from fighting.

Also, what seems to be overlooked is that rogues excel at hiding the way a wizard excels at spellcasting. This is a special ability of rogues that they can do better than any other character and the cunning action "hide during combat as a bonus action" was obviously put in there for a reason. You are essentially neutering the rogue if you take that ability away.

The rules say it right there, in black and white, that you generally can't get away with trying to sneak up on someone mid-combat unless the DM chooses to make an exception. Obviously the Rogue class was built with that in mind, so I'm not sure why you think enforcing the Stealth rules is "neutering the Rogue".

For the Arcane Trickster only 2 of the first 3 spells have to be Enchantment or Illusion. So it opens up the options for spells at first level a little. Shield for better defense, Fog Cloud, or Grease for area control during a fight, etc.

Wow! Thank you. I missed that little piece of information that only 2 of 3 opening spells have to be from Enchantment or Illusion. I have gone back and now I have Longstrider for my all out hit and run rogue.

"I'd like to add Dwarves to the list of good races to play rogues. If you are a dungeon delving group and want a trap & treasure finder I can't think of a better race. Bonus to Con, darkvision, stonecutting, and Dwarven Resilience (advantage & resistance to poison)... and if you take Hill Dwarf even more HP. "

Add Dungeon Delver Feat and your DM will FEAR you in any trap-based situation!

I came here just to see if there was anything I didn't think of, heheh. It's all stuff I'd thought about already, but this info would be super helpful to new rogues out there.

The combat stunt has always been something I've allowed in my games. I've never really made a set rule for it though. I usually just pick a DC on the fly based on how outlandish the stunt is. My rogue that I'm playing right now (Swashbuckler) is quite the exhibitionist (And a halfling, which makes it even funnier). I'll have her do somersaults and whatnot in combat, etc. I've come up with some pretty silly stunts just so she can make a point of being hardcore. (She is basically overcompensating for her small size, but she does it very well :D. I even have her stand in the saddle of her warhorse when travelling around town)

Thanks, that's pretty much my understanding as well. As you said a melee rogue cannot both disengage and hide with his bonus action so I would really see this mainly being a peek-around-cover, take a ranged attack, duck-back-behind-cover, and hide scenario.

It's more like jumping from behind the tank, stabbing for the sneak damage (don't need sneak attack for it only an ally next to it) and then disengaging to get back behind the tank